CA1040880A - Herbicide - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE:

This invention relates to herbicidal compositions of substituted pyrazolium salts and one or more active ingredients selected from the group consisting of benzothiadiazinone dioxides, phenol derivatives and phenoxycarboxylic acids. The compositions have a better action than their individual components while exhibiting the same good plant compatibility. These herbicidal compositions may be applied once or several times, inter alia after planting, postemergence or during emergence of the crop or unwanted plants. They are particularly suited for controlling mono-cotyledonous and dicotyldonous unwanted plants in crops.

Description

8~36) The present invention relates to new and valuable herbici-des consisting of synergistic mixtures of different active ingre-dients.
It is known that pyrazolium salts, dinitrophenol deriva-tives, hydroxybenzonitriles, hydroxybenzaldoxime aryl ethers, ben-zothiadiazinone dioxides and phenoxycarboxylic acids have a her-bicidal action. However, this action is not always satisfactory.
We have now found that a composition of:
a) a compound of the formula H O
C6H5~ C6H5 R_s_oe N-N O

where R denotes alkoxy, or phenyl which may be substituted by halogen or lower alkyl, and b) at least one compound selected from the group consist-ing of:
i) a compound of the formula l ~ ~2 i.
~ ~J~

~4~880 where R denotes lower alkyl and R denotes hydrogen, or a salt thereof (e.g., salts of ammonium, sodium, potassium,lithium, cal-cium, magnesium, ethylamine, dimethylamine, diethylamine, die-thanolamine, ethanolamine, dimethylethanolamaine and trimethyl-amine), ii) a compound of the formula ~ O-R , where X denotes chloro, bromo, iodo, nitro, cyano or lower alkyl, n denotes one of the integers 0, 1, 2 and 3, and R denotes hydro-.
gen, or a salt thereof ~e.g., the sodium and lithium salts), R

further denotes -C-alkyl, -C-N \ R , R2 and R3 denoting hydrogen, -lower alkyl or substituted or unsubstituted aryl, R further denotes , -N=CH ~ OR , -~-Y denoting chloro, bromo or iodo and Rl denoting lower alkyl, -C-alkyl or hydrogen, or a salt there-of (e.g., the sodium salt ), iii) a compound of the formula n ~ O-C~I-(CH2) -COO-R

or Xn Yn ~ O-CH2-Ca=CH-COO-R

-2-l~p4r~ 30 where X and Y denote chloro or methyl, n denotes one of the integers 0, 1, 2 and 3, R denotes hydrogen or lower alkyl, m de-notes one of the integers 0, 1 and 2 and Rl denotes alkyl or hydrogen, or a salt thereof te-g-, sodium,potassium, dimethyl-amine, diethanolamine and diethylamine), wherein the weight ratio of the compound (a) to the compound (b) is from 0.1 : 10 to 10 :
1 in the case of a 2-component mixture, and from 0.1 to 10 : 0.1 to 10 : 0.1 to 10 in the case of a 3-component mixture, has a better herbicidal action than its individual components.
The amount used of the compositions according to the inven-tion may vary and depends in essence on the type of effect to be achieved; it is generally from 0.1 to 30 (and more), preferably from 0.2 to 6, kg per hectare of active ingredient. The composi-tions according to the invention may be used one or several times before or after planting, before sowing, and before, during or after emergence of the crop plants and unwanted plants.
The compositions are selective in Triticum aestivum, Hordeum vulgare, Secale cereale, Zea mays, Oryza sativa, Pisum sativum, Phaseolus vulgaris, Solanum tuberosym, Glycine max. etc.
The compositions may also be used as total herbicides on ditches, aquatic areas, railroad tracks, and barren or waste land, etc.

-3-O.Z. 30,053 Application may be ef~ected ~or instance in the form o~
directly sprayable solutions, powders, suspensions~ disper-sions, emulsions, oil dispersions, pastes, dusts, broadcast-ing agents, or granules by spraying, atomizing, dusting9 broadcastlng of watering. The ~orms o~ application depend en-tirely on the purpose ~or whioh the agents are being used; ln any case they should ensure a ~ine dlstribution o~ the active lngredient.
For the preparation o~ solutions, emulsions, pastes and oil dlspersions to be sprayed direct, mineral oil ~ractions of medlum to hlgh boiling point, such as kerosene or diesel oil, ~urther coal-tar oils, etcO and oils o~ vegetable or mineral origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraf~in, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, `
cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulroxlde, N-methylpyrrolldone, water, etcO are suitableO
Aqueous ~ormulations may be prepared ~rom emulsion concen-trates, pastes, oll dlspersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredlents as suoh or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsiriers. Concentrates which are suitable for dilution with water may be prepared ~rom active ingredient, wetting agent, adherent, emulsi~ying or dispersing agent and possibly solvent or oil O

-4- `

1~4~88 O O Z ~ 30J 053 Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of lignlnsulfonic acid, naphthalene-sulfonic acids, phenolsulfonic acids, alkylaryl sulronates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of ~atty acids, salts Or sulfated hexadecan~s, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensatlon products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehydeJ polyoxyethylene octyl-phenol ethers, ethoxylated isooctylphenol, ethoxylated octy-phenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene,lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mlxing or grindlng the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous gra-nules, may be prepared by bonding the aotive ingredients to ~olid carrlers. Examples of solld ¢arriers are mineral earths such as sllloa gel, sillclc acid, sillca gels, silicates, talc, kaolln, Attaclay, limestone, lime~chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium su~ate, ~ $ ~ ~ OOZo 30,053 magnesium oxide, ground plastics, fertillzers such as ammonium sul~ate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain ~ours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
The formulations contain ~rom Ool to 95, and pre~erably 0.5 to 90, % by weight o~ active ingredientO
There may be added to the composltions or individual active ingredients (i~ desired, immediately before use (tankmix)) oils o~ various types, herblcides, ~ungicides, nemato¢ides, insecti-oides, bactericides, trace elements, rertilizers, anti~oams(e.g., silicones), growth regulators, antidotes and other herbi-cidally ef~ective compounds such as substituted anilines, substituted aryloxycarboxylic acids and salts, esters and amides thereo~
substituted ethers substituted arsonic acids and their salts, esters and amides substituted benzimidazoles substltuted benzisothiazoles substituted benzothiadiazinone dioxides -substltuted benzoxazlnes substltuted benzoxazlnones substituted benzothiadiazoles substituted blurets substltuted quinollnes substltuted carbamates substltuted allphatlc carboxyllc acids and their salts, esters and amides substituted aromatic carboxylic acids and their salts, esters and amides 1~4~880 - Z ~ 30,053 substituted carbamoylalkylthiol- or -dithiophosphates substituted quinazolines substituted cycloalkylamidocarbothiolic acids and their salts, esters and amides substituted cycloalkylcarbonamidothiazoles substituted dlcarboxylic acids and their salts, esters and amides substituted dlhydrobenzoruranyl sul~onates substituted dlsul~ldes substituted dipyridylium salts substituted dithiocarbamates .~ substituted dithiophosphoric aclds and thelr salts, esters and amldes substituted ureas substituted hexahydro-lH-carbothioates substltuted hydantoins substltuted hydrazides substituted hydrazonium salts substituted isoxazole pyrimidones substituted imidazoles substltuted lsothiazole pyrlmldones substltuted ketones substltuted naphthoqulnones substltuted allphatio nitriles substituted aromatic nitriles : :
substituted oxadlazole~ :
substituted oxadiazlnones substituted oxadiazolldine diones , :.

:, ' . . , ''. ', . ' '.. ~ ' ' ~ ; ' o.z. 30,05 1~4~880 substituted oxadiazine diones substituted phenols and their salts and esters substituted phosphonic acids and their salts, esters and amides substituted phosphonium chlorides substituted phosphonalkyl glycines substituted phosphites substltuted phosphorlc acids and their salts, esters and amldes substltuted plperldlnes substituted pyrazoles substltuted pyrazole alkylcarboxylic acids and their salts, esters and amides substituted pyrazolium salts substituted pyrazolium alkyl sul~ates substituted pyridazines substituted pyridazones substltuted pyridine carboxylic acids and their salts, esters ` and amides substituted pyridines substituted pyridine oarboxylates substituted pyridinones substltuted pyrimidlnes substltuted pyrlmidones -æubstituted pyrrolidlne carboxylic acld and lts salts, esters and amldes substituted pyrrolidines '.

1~4~880 -Z 30,o53 substituted pyrrolidones substltuted arylsulfonic acids and thelr salts, esters and amides substituted styrenes substituted tetrahydrooxadiazine diones substituted tetrahydroxadlazole diones substituted tetrahydromethanoindenes substituted tetrahydroxadiazole thiones substituted tetrahydrothiadiazlne thiones substituted tetrahydrothladlazole dlones substltuted aromatic thiocarbonylamides substituted thiocarboxylic acids and their salts, esters and amides substituted thiol carbamates ~: substituted thioureas substituted thiophosphoric acids and their salts, esters and r, amides substituted triazines substltuted trlazoles substltuted uraclls, and substltuted uretldlne diones.
im e last-mentioned herbicldal compounds may also be ap-plied be~ore or a~ter the active ingredients or compositions ~ thereo~ according to the invention.
`: m ese agents may be added to the herbicides accordin~
to the inventt.on ln a ratlo by welght of from 1:10 to 10:1.
me same applles to oils, ~ungicides, nematocides, insecti-cides, bactericldes, antidotes and growth regulators.

1~4~ 0 Z 30.05~
The new compositions have a strong herbicidal action and may therefore be used as weedkillers or for controlllng the growth or unwanted plants. Whether the new active ingre~dients are used as total br selective agents depends ln essence on the amount Or ingredient used per unit area.
By weeds and unwanted plant growth are meant all mono-cotyledonous and dicotyledonous plants which grow in loci where they are not desired.
The agents according to the invention may thererore be used for controlling ror instance ~ramineae, such as Cynodon spp. Dactylis spp.
Digitaria spp. Avena spp.
Echinochloa spp. Bromus spp.
Setaria spp. Uniola spp.
Panicum spp. Poa sppO
, Alopecurus spp. Leptochloa spp.
.. . .
Lolium spp. Brachiaria spp.
Sorghum spp. Eleuslne spp.
Agropyron spp. Cenchrus spp.
Phalarls spp. Eragrostis spp.
` Apera spp. Phragmites communls etc.;
Cyperaceae, such as Carex spp. Eleocharis spp.
Cyperus spp. Scirpus spp.
etc.;
dlcotyledonous weeds, such as ~4~880 -z. ~0,05~
Malvaoeae, e.g.
Abutilon theoprasti Hibiscus spp.
Sida spp. Malva spp.
etc.;
Composltae, such as Ambrosla sppO Centaurea spp.
Lactuca spp~ Tussilago spp.
Senecio spp. Lapsana communis Sonchus spp. Tagetes spp.
Xanthium spp. Erlgeron spp.
Iva spp. Anthemis spp.
Gallnsoga spp. Matricaria spp.
Taraxacum spp~ Artemlsia spp.
Chrysanthemum spp. Bidens spp.
Cirsium spp. etc.;
Convolvulaceae, such as -Convolvulus sppO Cuscuta spp.
; Ipomoea spp. Jaquemontia tamni~olia etc.;
` 20 Cruci~erae, such as ; Barbarea vulgaris Arabidopsis thaliana Brassica spp. Descurainia spp.
Capsella spp. Draba sppO
Sisymbrium spp. Coronopus didymus Thlaspi spp. Lepidium spp.
Sinapls arvensis Rapha~us spp.
etc.; -Geraniaceae, such as Erodium spp. Geranium spp.

O.Z. 30,053 etc,;
Portulacaceae, such as Portulaca spp. etc.;
Prlmulaceae, such as Anagallis arvensis Lysimachia spp.
etc .
Rubiaceae, such as Richardla spp. Dlodia spp.
aalium spp. etc.;
ScrophulariaQeae, such as Linaria spp. Digitalis spp.
Veronica spp. eto.;
Solanaceae, such as Physalis spp. Nicandra spp.
Solanum spp. Datura spp.
etc.;
UrticaQeae, such as Urtica spp.
Violaceae, suoh as Vlola spp. etcO;
Zygophyllaceae, such as Tribulus terrestris eto.;
Euphorbiaceae, such as Merourialis annua Euphorbla spp.
Umbelli~erae, such as Daucus carota Ammi ma~us Aethusa cynapi~m etc.;
Commellnaoeae, such as Commelina spp. etc.;

o . z . 30. 053 1~4~88V
Labiatae, such as Lamium spp. Galeopsls spp.
etc.;
Leguminosae, such as Medicago spp. Sesbania exaltata Trifollum spp. Cassia spp.
Vlcia spp. Lathyrus spp.
etc.;
Plantaginaceae, such as Plantago spp. etcO;
Polygonaceae, such as Polygonum spp. Fagopyrum spp.
Rumex spp. etc.;
Aizoaceae, such as Mollugo verticillata etc.;
Amaranthaceae, such as Amaranthus spp. etc.;
- Boraglnaceae, such as Amsinckla spp. Anchusa spp.
Myostls spp. Lithospermum spp.
etc.; -Caryophyllaceae, such as Stellaria spp. Silene spp.
Spergula spp. Cerastium spp.
Saponaria spp. Agrostemma githago Soleranthus annuus etc.;
Chenopodlaceae, such as Chenopodium spp. Atrlplex spp.

- ~:

.. . ...

-` o.z. ~0,05 1~4~8~0 Kochla spp. Monolepsis nuttalliana Salsola Kali etc.;
Lythraceae, such as Cuphea spp. etc.;
Oxalidaceae, such as Oxalls spp.
Ranunculaceae, such as Ranunoulus spp. Adonis spp.
Delphinium spp. etc.;
Papaveraceae, such as Papaver spp. Fumaria orficinalis etc.;
Onagraceae, such as Jussiaea spp. etc.;
Rosaceae, such as Alchemillia spp. Potentilla spp.
etc.;
PotamogetonaceaeJ such as - Potamogeton spp. etc.;
Na~adaceae, such as NaJas spp. etc.;
Equisetaceae Equisetum spp. etc.;
?: Marsileaceae, such as Marsilea quadrifolia etc.;
Polypodiaceae, Pteridium quilinum - 1~4~8~0 O~Z. 30,053 Alismataceae, such as Alisma spp. Sagittaria sagittlfolia etc.
In the greenhouse and in the open, compositions of the followin~ agents were tested on the abovementioned plants; it was ascertained that their action corresponds to that o~ the compositions in the examples below:
3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3-ethyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3-propyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3-isobutyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3-Isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethyl-amine salt 3-isopropyl-2,1,3-benzothladiazinone-(4)-2,2-dioxide, dietha~-amlne salt 3,5-dlbromo-4-hydroxybenzaldoxime-0-(2',4'-dinitrophenyl)-ether 3,5-dlbromo-4-hydroxybenzaldoxime-0-(2',4'-dinitrophenyl)-ether, sodium salt .
3,5-dlbromo-4-hydroxybenzaldoxime-0-(2'-¢yano-4'-nitrophenyl)-ether -`.`.
3,5-dlbromo-4-hydroxybenzaldoxime-0-(2'-nitro-4'-¢yanophenyl)-ether 3,5-dlbromo-4-hydroxybenzaldoxime-0-(2'-¢yano-4'-nitrophenyl)- .
ether, sodlum salt : .

1~4~880 o.z~ 30 053 3,5-diiodo-4-hydroxybenzaldoxime-0-(2'-cyano-4'-nitrophenyl)-ether 3,5-diiodo-4-hydroxybenzaldoxime-0-(2'-cyano-4'-nitrophenyl)-ether, sodium salt 3,5-dilodo-4-hydroxybenzonitrile 3,5-diiodo-4-hydroxybenzonitrile, lithlum salt 3,5-dliodo-4-hydroxybenzonitrile, sodium salt 3,5-dibromo-4-hydroxybenzonitrile 3,5-dibromo-4-hydroxybenzonitrile, sodium salt 3,5-dlbromo-4-octanoyloxybenzonitrile 2-methyl-4,6-dinitrophenol, sodium salt 2-sec-butyl-4,6-dinitrophenyl aoetate 2-tert-butyl-4J6-dinitrophenyl acetate 2-tert-butyl-5-methyl-4,6-dinitrophenyl acetate 2-isopropyl-3-methyl-4,6-dinitrophenol ; 2-sec-butyl-4,6-dinitrophenol, sodium salt 2-sec-amyl-4,6-dinitrophenol 2-(1-methylbutyl)-4J6-dinitrophenol 1,2-dimethyl-3,5-diphenylpyrazollummethyl sul~ate 1,2-dimethyl-3,5-diphenylpyrazolium-p-tolyl sulfonate a-(2,4-dichlorophenoxy)-propionic acid, dimethylamine salt a-(2,4-dichlorophenoxy)-propionic acid, sodium salt isooctyl a-(2,4-dichlorophenoxy)-propionate a-(2-methyl-4-chlorop,henoxy)-propionic acid, dimathylamine salt a-(2-methyl-4-chlorophenoxy)-propionic acid, diethanolamine salt a-~methylphenoxy)-proplonic acid, dimèthylamine salt -(2-methylphenoxy)-propionic acid, sodium salt 880 o.z. ~o, o5;~

isooctyl a-(2-methylphenoxy)-propionate a-(2,4,5-trichlorophenoxy)-propionic acid, potassium salt amyl a-(2,4,5-trichlorophenoxy)-propionate a-(4-chlorophenoxy)-propionic acid, dimethylamine salt a-(2-methyl-4-chlorophenoxypropionic acld, sodium salt a-(2-methyl-4-chlorophenoxy-propionic acid, potassium salt amyl 2,4,5-trichlorophenoxyacetate isooctyl 2,4,5-trichlorophenoxyaceta~e 2,4,5-trichlorophenoxyacetic acld, diethylamine salt 10 2,4,5-trichlorophenoxyacetic acid, potassium salt "
2,4- dichlorophenoxyacetlc acid, dimethylamine salt 2,4-dichlorophenoxyacetlc acid, sodium salt isooctyl 2,4-dichlorophenoxyacetate 2-methyl-4-chlorophenoxyacetic acid, dimethylamine salt isooctyl 2-methyl-4-chlorophenoxyacetate 4-chlorophenoxyacetic acid, dimethylamine salt 2-chlorophenoxyacetlc acid, dimethylamlne salt ~-(2,4-dlchlorophenoxy)-butyric acld, dimethylamlne salt isooctyl ~-(2,4-dichlorophenoxy)-butyrate ~-(2-methyl-4-chlorophenoxy)-butyric acid, sodium salt r-(2,4,5-trichlorophenoxy)-butyric acid, dimethylamlne salt ~-(4-chlorophenoxy)-butyric acid ~-(2,4-dichlorophenoxycrotonlc acid, dimethylamine salt ~-lsopropyl-2,1,~-benzothiadiazinone-(4)-2,2-dioxide, methyl-am~e salt 3-isopropyl-2,1,~-benzothiadlazinone-(4)-2J2-dioxide, tri-methylamine salt ~-isopropyl-2,1,~-benzothiadiazlnone-(4)-2,2-dloxlde, ethyl-amine salt -17- -:

, ' . ' .; .: . ' :. :, '' , , - 1~4~ -Z 30~05~

3-isopropyl-2,1,3-benzothladiazinone-(4)-2,2-dioxide, dlethylamine salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, ethanol-amine salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,a ~ ine ~t 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, pyridine salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, phenyl-enediamine salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, cyclo-hexylamine salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dodecyl-hexamethylenimlne salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, hydrazlne salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, magnesi-um salt, 3-isopropyl-2,1,3-benzothiadiazi~one-(4)-2,2-dioxide, calcium salt 3-lsopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, ammonlum salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, potassium salt 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, lithium salt 3-isobutyl-2,1,3-benzothladiazlnone-(4)-2,2-dioxide, sodium salt 3-isobutyl-2,1,3-benzothladlazlnone-(4)-2,2-dioxide, di-methylamine salt 1~4~ o.z. 30.053 3-isobutyl-2,1,~-benzothiadiazinone-(4)-2,2-dioxide, diethanol-amine salt 3 - sec-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 3-sec-butyl-2,1,~-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt 3-sec-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt 3-n-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 3-n-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethyl-amine salt 3-n-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanol-amine salt 3-n-propyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 3-n-propyl-2,1,~-benzothiadiazinone-(4)-2,2-dioxide, dimethyl-amine salt 3-n-propyl-2,1,3-benzothiadlazinone-(4)-2,2-dioxide, diethanol-; 20 amine salt 3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethyl-amine salt 3-methyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanol-amine salt 3-ethyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 3-ethyl-2,1,3-benzothladlazlnone-(4)-2,2-dloxlde, dimethyl-amlne salt .
~ .
- , . '' ' ; ' ' 1~4~8~0 Z- 30'053 3-ethyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanol-amine salt 3-sec-butyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3,5-dibromo-4-acetyloxybenzaldoxime-0-(2'-cyano-4'-nitrophenyl~
ether 3,5-dibromo-4-propionyloxybenzaldoxime-0-(2'-cyano-4'-nitro-phenyl)-ether 3,5-dibromo-4-phenylcarbamoyloxybenzaldoxime-0-(2'-cyano-4'-nitrophenyl)-ether 3,5-dlbromo-4-isopropylcarbamoyloxybenzaldoxlme-0-(2'-cyano-4'-nltrophenyl)-ether In the greenhouse, varlous plants were treated at a growth helght o~ ~rom 2 to 21 cm wlth the following amounts of the ~ollowlng lndividual active ingredients and composltlons there-o~ as oll dlspersions:
I 1,2-dimethyl-3,5-dlphenylpyrazollum methyl sul~ate II 1,2-dimethyl-3,5-diphenylpyrazollum-p-tolyl sul~onate III 3-lsopropyl-2,1,3-benzothladiazlnone-(4)-2,2-dioxide IV 3-i~opropyl-2,1,3-benzothladiazinone-(4)-2,2-dloxlde, ::
sodlum salt V 3-lsopropyl-2,1,3-benzothladlazlnone-(4)-2,2-dioxide, ~ -dlmethylamlne salt VI 3-lsopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt each Or these compounds at rates o~ 0.5, 0.75, 1 and 1.5 kg/ha;
I+III, I+IV, I+V, I+VI, II+IV and II+V
each o~ these composltlons at rates of 0.5+1, 1+0.5 and 0.75+0.75 kg/ha.
-20- i.

... . ~ .

~4~8~0 o.z, 30,053 Arter 12 to 15 days lt was ascertained that the compositions had a better herbicidal action than their components, combined with the same crop plant compatlbilityO
The results are given below:

o.z. ~0,05 U~
o o o o ~o ,,ooo ooo U~

OO J
oo o o ,~ 2 ,,o o o o ~o o oo o U~
H ~C) 1S~

O O O O O
OO O O O ~ CO~
~iO O O O ~ ~
_~O O O O O O
H ~O ~O
H ~O O OO 1~ 0 1~O O OO U~ o O 1~ 1~
~1 O O O ~ ~0 C~J
HO O O ~ CO

OO O O~ O l~ ." ' OO O O0~ 0 0 ',~ . .
a) ~1 ~
~1O O O ~ '' ;' ' H Ir\ O OO a~ ~ ) O

O O O O~ O ls~ h :`.

~ ~ Y a 5 ~

0 ~ ~ ,0 .,".., . .. .. . , - . '.'~
: , : .. . .

1~4~8t~0 o . %. 30, 053 U~ ~ o o o o ~ U~
~oc~ ~ 0 0 + ~ O O O U~ ~D
H ~--U~_ O O O t_ O

, ~, o o o r~
H ~> 0 0 + U~
H a~ 0 H Uo~ O O O 0 r-- O
~ O O O ~ O
H . ~ a~ 0 + U~ O O O O l~ ~
H Ir O 0 r-O` O O 0 0 O~
., ~, 00' O O O ~ ~ 00 H ~ Uo~ ~1 0 r-o o o O~ a) 8 t~ o o o o o o oo o~ a~ 0 + O O ~D ~
H u~ _ O O O 11~ t ~ : . :
o a~ ~ . .
H ~ ~ o o o o H ~ a~ 0 + ~ Il~ O O O r~ N
U` ~ 0~ 0 CO ' O O O O ~ 0 Il~
u~ 0 a~ o~
. O O O O O U~
,_ 0 0 : ' '.
O O O O ~ O .' 0~ O O O O ~ 0~ O

O O O O O U~ O ~
~ Ul :
P

b: D o ~ a R E
a~ :~ ~ ~ ~ ~ h ~ o ~ ~ ' oQI ~ d 3 ~ ~ ~ ~/ 11 11 h O ~ ~ ~, P 0 ~ o V Et m cq ~ ~ ~ o ,1 : -; -23-. . . , i . .
.. ,; ";` ,, , ., ,.~ - , ,.; ~ .. ~ .... .

~ 8 ~ 0 o,z. 30,053 In the greenhouse, various plants were treated at a growth height of from 3 to 25 cm with the following amounts of the ~ollowing individual active ingredients and compositions there-of as emulsions:
I 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate II 1,2-dimethyl-3,5-diphenylpyrazolium-p-tolyl sulfonate Dl 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide IV 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt 10 V 3-isopropyl-2Jl,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt VI 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt each o~ these compounds at rates o~ 0.5, 1.5, 2.5 and 3 kg/ha;
I+III, I+IV, I+V, I+VI, II+IV and II+V
each of these compositions at rates o~ 2.5+0.5, 0.5+2.5 and 1.5+1.5 kg/ha.

A~ter 14 to 18 days it was ascertained that the compositions had a better herbicidal action than their components, combined with the same orop plant compatibility.
The results are glven below:
-t~4~
o .z . ~o, o5:s o o o o g L~ o o o o o r~
N (~ (~
O O O O O O
~i ~D
O O O O O O
O ~ N
1~ O O O O IS~ ~
~ O O O O O O
N 0~ (~
~ ~ O O O O L-~ O

Ll~ O O O O O O
O ~ N
O O O O ~ IS~
CS~ (~
U~ O O O O O
H N ~ 0~
Ir~ O O O O L~ O
O O O O U~ O
.~ O 1~ 1 ~1 H ~1 U~ ~ ~ O O ~ O
N ~ I ~ H N
.~' H ~ o o o o o N
~1 U~ O O O O O O
.~ O ~
1~ 0 N O N
Ir~ o o o ~ Ll~ o . H (5~ H Nl lf\ O O O O O
.' ~i 0~ 1 O
O O O O ~ O Lt~ J~
J~
~ ~ ~ ~Q ~ Q~
~ .I S~ O ~Q) ~ bO ~>
~ .. o~ ~ ~ ~ ~
~P ~ ~ ~ ai n3 ~
~ ~ o ~ ~ ~ ~ ~o o , ~ ~ } ~ 1 ll ll J~ ~ O ~ O ~1 a) o c) bo ~ ~ O ~ ~: ~ td ~ O
C> E~ P ¢ ~ u~ O ~1 ~4~8~0 V ~ J ~J ~ ~
o o o o o o ~, o o o .

+ O N
H
H ~ ~ ~ O O Ir~ O
N O ~ O 0~ ~D
O O O O ~ O
. . O O O
~ ~ ~ ,_ ~. lr~ O O O N O O

H ~ . L~ t~ O O u~ 0 H N C~ . ~
OOO OOO
. O O O
~_ ~ ~ ~
H . O O O 1~ 8 ~ o~ ~ ~
H U~ U~ O O O O ~ O
. . o C5~ a~
C~l O ~
OOO OOO
. O O O
_~_ ~ ~ _ . ~ ~ O O
+ O C~l , , ~_ u~ O O O ~ O ~D O
. O O~ O~ .
C~l O ~
OOO OOO
. O O O
~ ~ ~ ~ ~ : .
OOO ~OO
H O c~.i 0 O O . . .
H 1~ 8 ~ a~
~, ~o ~
ooo ooo . . o o o ~ ~ . ~, ~_ ..
HH U~, O aD $ g + O C~l ~ _ . . .
,. U~l~ o o o o ~ ~
. o o~ o~ , :, . ~
~ o o o ~ 8 a~ ~
H . O O O O O O ~::
U~ O O O O O u~
_ OD aD
J~ `' O O O O 11~ 0 ~ .
~, O ~ ~ N a~ :
a~
~ ~D a a> ~ h 0 ~ R ~ ~ a .. ~ ~ ~0 0 0 ~ ~ ~ ~ i u2! 0 ~ ~D h h El ~ Q, ~rl J~ 0 ~ ~ ~ ~d ' a~ ~ ~ .. ~0 0 ~ ~ o :~ td ~ ~ ~ h ~1 ~ ~ O ~ ~ E3 0 11 11 C) ~ Q ~ ~ O
v h h O ~ ~ O

8 ~ 0 O.Z, 30,053 In the greenhouse, various plants were treated at a growth height of ~rom 2 to 21 cm with the rollowing amounts of the ~ollowing individual active ingredients and compositions thereof as dispersions:
I 1,2-dimethyl-3,5-diphenylpyrazolium methyl sul~ate II 1,2-dlmethyl-3,5-dlphenylpyrazolium-p-tolyl sulfonate V 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, dimethylamine salt VII 2-sec-butyl-4,6-dinitrophenyl acetate o vm ~, 5-diiodo-4-hydroxybenzonitrile IX 3,5-dibromo-4-hydroxybenzaldoxime-0-(2',4'-dinitro-phenyl)-ether X 3,5-dibromo-4-hydroxybenzaldoxime-0-(2'-cyano-4'-nitro-phenyl)-ether, sodium salt each of these compounds at rates of 0.25, 1 and 1.5 kg/ha, I+V+VII, I+V+VIII, I+V+IX, II+V+VII, II+V+VIII, II+V+IX and I+V+X
each o~ these compositions at rates o~ 1+0.25+0.25, 0.25+1~ æ5 and 0.25+0.25+1 kg/ha.
; 20 A~ter 12 to 16 days lt was ascertalned that the composl-tions had a better herbicidal action than thelr components, combined with the same crop plant compatibility.
m e results are given below:

o.z-u~o o o o o o ~ o o ~ ~o o o o u~ 0 ~ O O O O 11~ 0 ~ o o o o ~ ~

U~ OOO OOO
H ~ ~ t--p~ ~ O O O O O U~
NO O O O I
Il~O O O11~ 0 IS~
H U~
~OOO OOO
O O OO CO O
O ~ N
.
,.O O O O O O
~ U~ ~
.C~ O O O O 1 O N N
11~ O O O O O N
~ 0 ~ . ' H - O O O N Ir~ 0 N O O O aD O O
~O O 0 00~0 ~ ~ .

H .O O O 11~ ~D O
OO O O O O O a -- c ~~, 5 ~ ~ ~

~c ~ ~ , O O ' ~ ~ ' 7I h ~ 0 ~ ~ O

O.Z. 30,053 ~U~
N N O O O O U~ O
O O 0 ~0 0 H Ir~
N O O O O O O

H_ O O O ~ O ~O

XU~ U~
~; O O O O O N g g U~l~
N N O O O ~ O O
N N $ 0~ g O O ~-- O O
O O ~ ~ H 11~
1~ + N N O O O QQ O O
O O O O g g + O O t-- O O
O O ~ H
N ~ O O O O ~ ~--t~ O ~ O O O O O g ~ O O O a~ 0 O O O O O g O ~ H r- 0~ 0 ` H O O ~ 0~ 8 + o o + O O ~-- _ H 11~ In O O O 0 ?? ~ 8 o o ~ ~
NN O O O N O O
O O CO O O
H U~ ~
N _ O O O 11~ ~ ~D

H U~ rl o o ~OD co ~ ~ +~

3 ~ C b !~

1~4'~ o.z . 30,05~

In the open, various plants were treated at a growth height of from 2 to 18 cm with the rollowing amounts Or the followlng indlvidual active ingredients and compositions ; thereo~ as emulsions:
I 1J 2-dimethyl-3,5-diphenylpyrazolium methyl sul~ate III 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide IV ~-lsopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt V 3-lsopropyl-2,1,3-benzothladiazinone-(4)-2,2-dloxlde, dlmethylamlne salt VI 3-lsopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dloxlde, -dlethanolamine salt XI a-(2-methyl-4-chlorophenoxy)-proplonic acid, dimethyl-amine salt XII a-(2,4-dichlorophenoxy)-propionic acld, dlmethylamine salt xm a-(2,4,5-trichlorophenoxy)-propionic acid, potassium salt ` XIV 2-methyl-4-¢hlorophenoxyacetic acid, dimethylamine salt XV 2,4-dichlorophenoxyacetic acld, dlethanolamlne salt XVI 2,4,5-triohlorophenoxya¢etic acld, potasslum salt ; 20 each Or these compounds at rates Or 0.5, 1,2 and 3 kg/ha;
III+I+XVI, IV+I+XIII, V+I+XI, V+I+XII, V+I+XIV and VI+I+XV
each Or these composltions Or rate o~ I+l+l, 0.5+2+0.5, 2+0.5+0.5 and 0~5+0.5+2 kg/ha.
After 14 to 17 days lt was ascertained that the composi-tlons h~d a better herblcidal action than their components, combined with the same crop plant compatibillty.
me results are glven below:
-3o-1(~4~8~0 -Z- ~ 05 o o o ~ 8 C~l o o o o U~

~O
O O O O U~ O
O t~
O O O O O U~
o a~
N O O O O ~ O
0 a~
O O O O O O
U~
Il~ O O O O O O
O ~ N
O O OO l~ N
N O O OO 11~ 0 ~ aD
H ~ O O OO O
~O It~
U~ O O O O O O
O t~ N
~ O O O O L~ ., H C~l o o o O u~ N
O O O O O O
U~ O O O O ~ O
O ~
I<~ I~ O C~lO ~ O
O C~
~I O O O O 1 H 3~ ~ ~
~ O O O U~ ~D O
~ .
o O O O ~ O U~

~ ~ Q~
.~ ~ h a a~ 0 ~ ~ .
~1 D ~ ~1 3 ~ ~ ~
Q ~ ~ 1l 1l O ~ ~ ~ O O
o ~J h h o ~ ~ t~ ~ ~ O
~ ~ V E~ ~ ~_ .

` o.z. ~0,05 i~4~B8~
~ o o oo o~ o X ~ O O O O O O
U~ O O OO O U~
O' ~ O O O ~t N O O OO ~-- 0 N 1~
O O O O O O
N N
O O O O O U~
o ~_~
O O O O O O
I~ O O
H N O O O O U~
" '- O O OO t- O
U~
O ~t U~
~0 ~

~ o o oo U~ o . ~
~ . `:
O O O OO O O ~ , ~ ~ ~o ~o H O O O1~ O : ~ ~
O O OO O U~ ..
Ir~ ~
~ O O OO ~ ~

c ~h 1~ R
bO ;~ ~ ~3 h o E
~ ~ ~ ~~ ll ll to ~ Y ~1 ~ ,~ oO

- ~2 -, . , ., ~ .

1~4~8~30 -Z 30'053 Uo~ Uo' N

X O O ~ ~
H 11~ 1~ O O O O O N
' O O O O
O O O O O O
O O O
~ ~ ~_ o o ~ o 8 + U~ U~ O

~-~o o o o o o o o o o o Y o o o o 8 . ~ . O O o O
H O O
~.- O O O O O O
~ O O O O O
C~l ~ ~ O O

+O O t-- O O

H O O O O O O O O
~-O O O O O O
O O O
1~ 0~ ~ ~~ o O
~J t- O O O O O
H'' ~ ~ O`
~¢O O O O O O
~U~

1~

~1 ~ h ~ O O

' o.z. ~o>o~

~0~8E30 o o o ~ o . . ~ t- o a~
oo ~ . .
o o o o o o ~ ~oo ~ o o . -H
H m U~ O O O O N OD
~ 0~0 O ~ ~ ~'.
.` ~ O O O O O O
O O O ..
U~ O O O O N O
. . ~1 1~ O~ O
00 ~
O O O O O O
. . r-- o o ~` X 00 + U~ O O O O O C~
.. p~, ~ . o a~
., O O ~
~ o 8 o ~ . ~ .

~ ~ ~ ~ R ~ ~ ll ll ~ ~P ~ h C~ 0 ~

..
4 -- .

1~4~880 o . z, 30, 05~

In the greenhouse, various plants were treated at a growth height of ~rom 2 to 18 cm with the following amounts o~ the following individual active ingredients and compositlons there-of as solutions:
I 1,2-dimethyl-~,5-dlphenylpyrazolium methyl sulfate VII 2-sec-butyl-4,6-dlnitrophenyl acetate XII ~-(2,4-dichlorophenoxy)-propionic acid, dimethylamine salt each Or these compounds at rates o~ 0.5, 1 and 2 kg/ha;
I+VII+XII at rates o~ 1+0.5+0.5, 0.5+1+0.5 and 0.5+0.5+1 kg/ha.
A~ter 14 to 16 days it was ascertained that the composl-tions had a better herbicidal action than their components, combined with the same crop plant compatibility.
The results are given below:

' .
.

. -" .
"
:

. ~

, , .

-- 0.2. 30,053 1~4 ooo ooo . . _ r- o oo ~
H O O O CS~ ~ O
+ ~ ~ ~ ~ O~ OD
H O O
O O O O C~ ~9 ~ ~ . . O ~
00 ~
N O O O lr~ O O
OD C~l .. '' H ~ O O O O U~ O
H ~
O O O O O O
O N

C~l O O O O If~ O
H ~ ~ It~
H ~ O O O O

U~
.' O O O O O U~ O

~ O O O O ~ ~D

:` H ~ O O O U~ ~D O
, ~D ~ ~ "" .
: ~ ~
O O O O lr~ O 11~ t~

~ h ~ bO a) I In ~ e ¦ ~ ~
~ ~ ~0 ~ ~ D 00 '' ' ` o~D h o ~ I e- ~d ~ O
cC ~ ~ E~ ~ ~ '.
36- ~ ~

1~4'~880 .z . 30,053 In the greenhouse, various plants were treated at a growth height of from 2 to 24 cm with the ~ollowing amounts of the following indivldual active ingredients and compositions there-o~ as emulsions:
I 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate VII 2-sec-butyl-4,6-dinitrophenyl acetate vm 3,5-diiodo-4-hydroxybenzonitrile, lithium salt IX 3,5-dibromo-4-hydroxybenzaldoxime-0-(2',4'-dinitrophenyl)-ether, sodlum salt X 3,5-dlbromo-4-hydroxybenzaldoxime-0-(2'-cyano-4'-nitro-phenyl)-ether, sodlum salt XI a-(2-methyl-4-chlorophenoxy)-propionic acid, dimethylamine salt XII ~-(2,4-dichlorophenoxy)-propionic acid, dimethylamine salt ~:
xm a-(2,4,5-trichlorophenoxy)-propionic acid, isooctyl ester XIV 2-methyl-4-chlorophenoxyacetic acid, dimethylamine salt XV 2,4-dichlorophenoxyacetic acid, dimethylamine salt :~
XVI 2,4,5-trichlorophenoxyacetic acid, isooctyl ester -XV~ ~-(2,4-dichlorophenoxy)-butyric acid, dimethylamine salt XVIII 3,5-dibromo-4-hydroxybenzonitrile, sodium salt each of these compounds at rates o~ 0.5, 0.75, 1 and 1.5 kg/ha;
I+VII, I+VIII, I+IX, I+X, I+XI, I+XII, I+XIII, I+XIV, I+XV, . I+XVI, I+XVII and I+XVIII .
each of these compositlons at rates o~ 0.5+1, 1+0.5 and 0075+ :
0.75 kg/ha.
A~ter 12 to 15 days it was ascertained that the compositions had a better herbicidal action than their components, combined with the same crop plant compatibility.
. m e results are given below:

.. , ,, r .

o~ z~ ~cJ o5~

1~4~880 o o a~ u~
. . o~ 0 a~

U~ O O O ~ O
~+ O O ~ 0 H U~
. ~ O Ir~ 0 ~1 N O
o ~ o t- ~ a0) ~D u~

o o o o ~ ~
+ O O L~
H
U~ O O O ~ 0 O 0 U~ U~
~_~ o o o a~ o 0 . . aD O~ U~
H

O O O O O O
+ O 0 0 ~>
H

. ~ O O O C~l 0 O 0 O~
t--~ O O O 0~ N
00 0 ~
+ O O O O
H O O U~
U~
.~_ O O O O O
O 0 ~ U~
U~ 1~
O 0 0 0 ~ 0 . . 0 .. ~ U~
H O O O O 0 0 U~ .~ :
O O O ~I O ~ o O ` 0 ~D ~D ~ .
~ ~ '.
h ~I
0 ~ h ~ ~ X .
~ ~ ~ ~ ~ ~ ~ .
~ ~ ~ 0 ~ ~1 ~I 11 .C ~ ~ 0 ~ P ~ ~1 - ! ~ ~1 h C) ~d ~ ~ ~> O O
~ h ~ æ ~ ~ ~ ~o C. Z. 30, 5:~

1`~4~880 ~r- o o o ~ ~ o O O ~ O~
H 15~ O O O 0 1~ 15 + O O aD Gt) U~ U~ ~ O ~ O O
O ~ O O
~r- o o o ~ o o H O O ~0 0 ) ~ ~ ~ O ~
H O ~
O O C~) Ir~ I
o o o o~ o o~
H CO C~ t--X l~ O O O O ~D O
H O O t--., O O O '- O
O C~
~r- O o o co o o a~
O O O O O ~ :
H O . O OD CO
O ~ ~0 ~ ':
~r- O O 0 0 0 ~ :~-X oo Ot~ ~
H U~
,~, ~ . O O O O ~ O
o o r- ~D
0~ O O a) 0~ ~
~ t~ ~ .
s:: ~ t a~
+~ 0 ~ ~ ~
u H u R ~ h ~ 4 0 ~ o 3 o ~ 0 ~3 ~ 1l 1l c~ OD ~ ~ p 0 a) o O

_ ;~9 _ - Z 3 0, 05 ~4~8~30 ~ t-- ~

H Ir~ O O O O ~) N
O O ~
H
, _ O O O
O ~ ~ N 0 ~ /5 . . o o o a H
H u~
~ ~- . O O O O ~D C
+ o o t-- a~
o o C~ a~) l-~ N ~D O O ~ ~
~D ~
~ O ~ aD O O O
H U~
H t-- r-. ~ ~ O ~ 1 Ir~ Ir~ O O O O Ll~ :
O N N
.. Il~ O O O O Ll~
N ~--H ~ O O O O CD CD
H
''"` X U~
:~ ~ O O OO u~ ~D
:~ O ~ ..
U~ O O O O N 1~
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~ ~ OOO OOO
.~ ~ ~ N
~ U~ ., .~. . O O O O U~ ~D
O
Ir~ ., O O O O 0 0~ 0 +~
~ ~ .
~ ~Q

P ~ Q) ~d ~ 'ql ~1 ~ a ~ ~ .
~4 0'~ h ~ ~ ~ ~ ~
C~ ~ ~ ~ o ~ ~.
0 ~ ,~ il 11 ;
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,`- .,, ~ o ~ ~ ~ ~ ~ O O
a u ~ ;t~ ~ ~ ,0 .~. .
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;

; . ... ... ~ ... ; . ;, , O.Z.30,~53 1~4~880 U~ o o o o ~ o N N
~ O O O O O O
P N ~
o o o o u~ a~
C~
U~ O O O O O U~ .`
O
U~ O O O O U~ U~
~- N 1<~
~ ~ O O O O O O
H O O O O U~ 0 C:~
U~ O O O O O Il~
O __ U~ O O N O Ir~ U~
~ ~ _ 0 0 H _li~ t-- O ~ O U~
H ~ ~D
~¢ ~ O O O O ~ O
O ~ :
U~ O O O O O O
O ~ ~ . `
U~ O O O U~ '.
_ ~ r- ~ ::
_O O O O IS~
H ~ 1~
~o o o o ao ~t U~O O O O O U~
O ~ ~
U~O O O O O O
:`
~ O O O O O U~

OO ~ O O ~ ~
~. O 000 00~ ~;

P ~ a> ~ ,.:
0 h El ~ a ~

h h 0 ~ O oO

- 41 - ;:

,, ~, . `: . ,: " ` ` ` `

1~4'~880 Z- 30'053 U~o o o o o o ~ o o ~ o o o o o o u~ a~ o~
o o o o o U~
o o o o o o~ ~
U~o r~ o o o o . ~ ~ ~ ~ r-o o o o o 0 ~C U~ ~
H ~_o o o o Lt~ 11 O ~t ~
O O O O O ~ ~ . '.
I~ O O O O O O
C~ N t-- 0 )-I ~O O O O O 1 H ~ ~ ~
t~ ~ 0 O U~
. O O O O O O
O ~ .' . O O O U~ O U~ .' If~ r-O O O C~l U) O
H ~ ~ ~D
t~
O
1~
O O O O O ~ ~ ... ~, 0 ~ :` ~
,. O O O U~ ~D O ., ~ ~ . ', ~ ~ O O 0 0 U~ O ~ .

O O O O ~ O U~
El C ~ 6 ~. ~ ~ 0r~1 11 11 ,,, ~~ ~ ~ 0 ~:
~ ~ 0 ~1 ~D O O
u toI ~ q' ~ P 0 ~ o 's ~ c~ ~ w u~ ~ "~

- ~2 - :

' 1~4~880 o.z. ~0,05~

In the greenhouse, various plants were treated at a growth height of from 2 to 20 cm with the ~ollowing amounts of the following individual active ingredients and compositions there-Or as dispersions, emulsions, solutions and tankmixes:
I 1,2-dimethyl-3,5-diphenylpyrazollum methyl sulfate III 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide IV 3-isopropyl-2,1,3-benzothiadiazlnone-(4)-2,2-dioxide, sodium salt . V 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxlde, dimethylamine salt VI 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt VII 2-sec-butyl-4,6-dinitrophenyl acetate VIII 3,5-diiodo-4-hydroxybenzonitrile, sodium salt IX 3,5-dibromo-4-hydroxybenzaldoxime-0-(2',4'-dinitrophenyl)-ether , X 3,5-dibromo-4-hydroxybenzaldoxime-0-(2'-cyano-4'-nitro-phenyl)-ether, sodium salt XI a-(2-methyl-4-chlorophenoxy)-propionic acid, dimethylamine salt XII a-(2,4-dichlorophenoxy)-propionic acid, sodium salt XIII a-(2,4,5-trichlorophenoxy)-propionic acid, potassium salt XIV 2-methyl-4-chlorophenoxyacetic acid, dimethylamine salt XV 2,4-dichlorophenoxyacetic a¢id, dimethylamine salt .
; XVI 2,4,5-trichlorophenoxyacetic acld, potassium salt -.
' XVII ~-(2,4-dichlorophenoxy)-butyrlc acid, dimethylamine salt ~ :
xvm 3,5-dibromo-4-hydroxybenzonitrile, sodium salt each o~ these compounds at rates o~ 0.25, 1 and 1.5 kg/ha;
_43-: .

- 1~4$880 30, I + III + VII, T + III + VIII, T + III + IX, I + III + X, I + III
+ XI, I + III ~ XII, I + III + XIII, I + IIi + XIV, I + III + XV, I + III + XVII, I + IV + XI, I + IV + XII, I + IV + XIV, I + IV +
XV, I + IV + XVI, I + IV + XVII, I + V + VII, I + V + VIII, I +
V + XVIII, I + V IX, I + V + X, I + V + XV, I + V + XVI, I + V +
XVII, I + VI + VII, I + VI + VIII, I + VI + IX, I + VI + X, I +
VI + XI, I + VI + VIII, I + VII + XI, I + VII + XII, I + VII +
XIII, I + VII + XIV, I + VII + XV, I + VII + XVI, I + VII + XVII, I + VIII + XI, I + VIII + XII, I + VIII + XIII, I + VIII + XIV, I + VIII + XV, I + VIII + XVI, I + VIII + XVII, I + XVIII + XI, I + XVIII + XII, I + XVIII + XIII, I + XVIII + XIV, I + XVIII +XV, I + XVIII + XV, I + XVIII + XVII, I + IX + XI, I + IX + XII, I + IX + XIII, I + IX + XIV, I + IX + XV, I + IX + XV, I + IX +
XVII, I + X + XI, I + IX + XII, I + IX + XIII, I + IX + XIV, I + IX + XVt I + IX + XV, I + IX + XVII, I + X + XI, I + X + XII, I + X + XIII, I + X + XIV, I + X + XV, I + X +XVI, I + X + XVII, III + VII + XI, III + VII + XII, III + VII + XIII, III + YII +
XIV, III + VII + XV, III + VII + XV, III + VII + XVII, III +
VII + XI, III + VIII + XVII, III + VIII + XIII, III + VIII +
XIV, III + VIII + XV, III + VIII + XVI, III + VIII + XVII, III + IX + XI, III + IX + XII, III + IX + XIII, III + IX + XIV, III + IX + XV, III + IX + XV, III + IX + XVII, III + X + XI, III + X + XII, III + X + XIII, III + X + XIV, III + X + XV, III + X + XVI, III + X + XVII, IV + VIII + XI, IV + VIII + XII, IV + VIII + XIII, IV + VIII + XIV, IV + VIII + XV, IV + VIII +
XVI, IV + VIII + XVII, IV + IX + XI, IV + IX + XII, IV + IX +
XIII, IV + IX + XIV, IV + IX + XV, IV + IX + XVI, IV + IX + XVII, IV + X + XI, IV + X + XII, IV + X + XIII, IV + X + XIV, IV + X +
XV, IV + X + XVI, IV + X + XVII, V + VII + XI, V + VII + XII ?
V + VII + XIII, V + VII + XIV, V + VII + XV, V + VII + XVI, V + VII + XVII, V + VIII + XI, V + VIII + XII, V + VIII + XIII, V + VIII + XIII, V + VIII + XV, V + VIII + XV, V + VIII + XVII, V + IX + XI, V + IX + XII, V + IX + XIII, V + IX + XIV, V + IX I
XV, V + IX + XVI, V + IX + XVII, III + XVIII + XI, III + XVIII +
XII, III + XVIII + XIII, III + XVIII + XIV, III + XVIII + XV, III + XVIII + XVI, III + XVIII + XVII, IV + VII + XI, IV + VII +
XII, IV + VII + XIII, IV + VII + XIV, IV + VII + XV, IV + VII +
XVI, IV + VII + XVII, III + XVIII + XI, III + XVIII + XII, III + XVIII + XIV, III + XVII + XV, III + XVIII + XVI, III +
XVII + XVII, V + X + XI, V + X + XII, V + X + XIII, V + X + XIV, V + X + XV, V + X + XVI, V + X + XVII
_41~_ ~ 1~4~B80 o.z. ~0,053 each o~ these compositlons at rates of 1+0.25+0.25, 0.25+1+0.25 and 0.25+0.25+1 kg/ha.
After 12 to 15 days it was ascertained that the composi-tions had a better herbicidal a¢tion than their components, combined with the same crop plant ¢ompatibility.
The results are given below:

'' 0'. '' ~:

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. ' '' :
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~o ~ 4~880 o.z. 30,053 In the greenhouse, various plants were treated at a growth height Or rrom 2 to 20 cm with the following amounts of the following individual active ingredients and composi-tions thereo~:
I 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate III 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide IV 3-lsopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, sodium salt V 3-isopropyl-2,1,3~benzothiadiazinone-(4)-2,2-dloxide, dimethylamine salt VI 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide, diethanolamine salt XI a-(2-methyl-4-chlorophenoxy)-propionic acid, sodium salt XII a-(2,4-dichlorophenoxy)-propionic acld, dimethylamine ~ -salt XIV 2-methyl-4-chlorophenoxyacetic acld, dimethylamine salt XV 2,4-dichlorophenoxyacetic acid, dimethylamine salt XVI 2,4,5-trichlorophenoxyacetic acid, isooctyl ester -each o~ compounds I to VI at rates of 0.5 and 1.5 kg/ha, and each of compounds XI to XVI at rates of 0.25 and 1.5 kg/ha;

.. . ...

lV 4~ 8 ~ V 0.z. ~o,o53 I + III + XV ~ XIV, I + IV + XV + XIV, I + V + XV + XIV, I + VI ~ X~ XlV, I + III + XV + XI, I + IV + XV + XI, I + V I ~V ~ XI, I -: VI _L XV + XI, I + III + XI + XVI, I + IV + XI + XVI, I + V + XI + XVI, I + VI + XI + XVI, I + III + XV + XVI, I + IV + XV + XVI, I + V + XV + XVI, I + VI + XV + XVI, I + VI + XIV + XVI, I + IV + XIV + XVI, I + V + XIV + XVI, I + VI + XIV + XVI, I + III + XII + XVI, I + IV + XII + XVI, I + V + XII + XVI, I + VI + XII + XVI
each of these compositions at a rate o~ 0.5+0.5+0.25+0.25 kg/ha.
After 12 to 15 days it was ascertained that the com-positions had a better herbicidal action than their com-ponents~ combined with the same crop plant compatibility.
The results are given below:

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Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A herbicidal composition comprising a synergistic mixture of:
a) a compound of the formula:

, where R denotes alkoxy, or phenyl which may be substituted by halogen or lower alkyl, and b) at least one compound selected from the group consisting of:
i) a compound of the formula:

, where R denotes lower alkyl and R1 denotes hydrogen, of a salt thereof, ii) a compound of the formula:

, where X denotes chloro, bromo, iodo, nitro, cyano or lower alkyl, n denotes one of the integers 0, 1, 2 and 3, and R denotes hydrogen, or a salt thereof, R further denotes , , R2 and R3 denoting hydrogen, lower alkyl or substituted or unsubstituted aryl, and R further denotes , Y denoting chloro, bromo or iodo and R1 denoting lower alkyl, or hydrogen, or a salt thereof, iii) a compound of the formula:

or , where X and Y denote chloro or methyl, n denotes one of the integers 0, 1, 2 and 3, R denotes hydrogen or lower alkyl, m denotes one of the integers 0, 1 and 2, and R1 denotes alkyl or hydrogen, or a salt thereof, wherein the weight ratio of the compound (a) to the compounds (b) is from 0.1 : 10 to 10 : 1 in the case of a 2-component mixture, and from 0.1 to 10 : 0.1 to 10 :
0.1 to 10 in the case of a 3-component mixture .